Perhaps the biggest swing and miss in the Manny Machado sweepstakes came from the windiest of cities, a franchise that has whiffed on myriad things the last decade and a half: the Chicago White Sox.

Machado’s record 10-year, $300 million deal with San Diego on Tuesday left the Sox and their fan base in a sour mood, and with good reason. Since winning the World Series in 2005, seemingly nothing has gone right for the South Side of Chicago.

The White Sox have been to the playoffs just once in the last 13 seasons. They haven’t finished over .500 since 2012. The closest they’ve come to winning the AL Central in the last six seasons was in 2016 when they finished 16 1/2 games behind Cleveland. The rival on the north side of town has been to the playoffs four years in a row and is trending toward a fifth.

Chicago South even went the creative route in recruiting Machado, trading for his brother-in-law Yonder Alonso and best friend Jon Jay.

Compounding matters, Ken Rosenthal of The Athletic reported that the Sox made an eight-year, $250 million offer with $100 million in incentives to Machado — a better yearly offer than the Padres'.

Machado joins a San Diego infield rife with talent, highlighted by Fernando Tatis Jr., the No. 2 prospect in baseball. Ironically, Tatis is a former White Sox prospect whom Chicago signed as an international free agent in 2015, only to trade him to San Diego for pitcher James Shields in 2016. Shields went 4-12 with a 6.77 ERA that season. He also led the majors in home runs allowed (40) and home runs per nine innings (1.98) and had the league’s highest WHIP (1.48).

White Sox executive vice president Ken Williams said Tuesday he was "in a little bit of disbelief" that Machado turned down their deal. Had Machado signed with Chicago, his contract would have far exceeded the current most lucrative contract in team history — Jose Abreu’s six-year, $68 million deal signed in 2013.

Ken Williams on the White Sox missing out on Manny Machado: "I feel we put our best foot forward."

While news of Machado opting for sunny beaches over a city still recovering from a polar vortex stings in 2019, there’s reason for fans to be optimistic that 2020 is, and always was going to be, the Sox's year, regardless of whether Machado was playing third base for them.

The team had been experimenting with playing Yoan Moncada at third base as recently as Monday. Chicago’s farm system is one of the best in baseball. MLB.com ranks it as the third-best in the game, with six of the top 100 prospects — outfielder Eloy Jimenez (No. 3), right-hander Michael Kopech (No. 18), pitcher Dylan Cease (No. 21), outfielder Luis Robert (No. 40), infielder Nick Madrigal (No. 47) and right-hander Dane Dunning (No. 80).

Kopech received his long-anticipated call to The Show last August and appeared in four games before tearing the ulnar collateral ligament in his pitching elbow. He underwent Tommy John surgery and has been ruled out for the 2019 season.

Kopech’s 100-plus mph heater wouldn’t have been available for Machado’s first season, and one of the minors' best sluggers, Jimenez, would not have been with him on Opening Day.

In 108 games with Double-A Birmingham and Triple-A Charlotte last year, Jimenez hit .337/.384/.577 with 22 home runs and 75 RBIs.

"I look at him as the Babe Ruth of our generation," Kopech said of Jimenez on Saturday.

As great as Jimenez is, he won’t be called up to the majors until late April 2019 at the earliest because of service-time rules that will allow the White Sox to control him contractually for an additional year.

With Chicago's young talent, a blockbuster free-agent addition this winter was never a requisite for future success. The White Sox's projected 2019 payroll is less than $80 million, ranking them 25th in baseball, and they'll have about $40 million coming off the books next offseason.

White Sox general manager Rick Hahn told reporters that money not used on Machado "will be spent. It might not be this offseason, but the money will be spent."

If the White Sox wanted, they could still go out and sign a pitcher like Dallas Keuchel or Craig Kimbrel, or the versatile Marwin Gonzalez to bolster their infield, but it may be smarter to hang tight for one more year and acquire another top-five draft pick. With the bulk of their top prospects being outfielders, a deal with Bryce Harper would appear unwise.

So, no, Machado signing with San Diego is most definitely not a positive, but aren't good things supposed to come to those who wait? The White Sox have done a lot of waiting, so what’s one more year?